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Synthesis 1997; 1997(12): 1389-1390
DOI: 10.1055/s-1997-1367
short paper
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Studies on Isocyanides and Related Compounds. An Unusual Synthesis of Functionalized Succinimides

Ricardo Bossio1 , Carlos F. Marcos2 , Stefano Marcaccini3 , Roberto Pepino1
  • 1CNR, Centro di Studio sulla Chimica e la Struttura die Composti Eterociclici e loro Applicazioni, Dipartimento di Chimica Organica “Ugo Schiff”, Universitá di Firenze, via Gino Capponi 9, I-50121 Firenze, Italy
  • 2Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, E-10071 Cáceres, Spain
  • 3CNR, Centro di Studio sulla Chimica e la Struttura die Composti Eterociclici e loro Applicazioni, Dipartimento di Chimica Organica “Ugo Schiff”, Universitá di Firenze, via Gino Capponi 9, I-50121 Firenze, Italy, E-mail: marc@risc1.chimorg.unifi.it
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Publication History

Publication Date:
31 December 2000 (online)

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The treatment of (E)-2-[(N-chloroacetyl-N-(4-nitrophenyl)amino]-4-phenylbut-3-enoic acid N-cyclohexamide (6a) with KOH does not afford the expected β-lactam 1a but the succinimide 7a, probably through a ring enlargement of compound 1a itself. A hypothesis on the reaction mechanism, which is corroborated by experimental results, is formulated.

isocyanides - Ugi four-component condensation (4CC) - β-lactams - ring enlargement - succinimides